


Wanna Try Something With Me?

by memoriesofrain



Category: Until Dawn (Video Game)
Genre: Anal, Anal Fingering, Anal Sex, Best Friends, First Time, Fluff and Smut, Friends to Lovers, Fun, Idiots in Love, Kinktober, Kinktober 2019, M/M, Sex, Sexual Humor, Teasing
Language: English
Status: Completed
Published: 2019-10-16
Updated: 2019-10-16
Packaged: 2020-12-20 16:27:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,058
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21059666
Author URL: https://archiveofourown.org/users/memoriesofrain/pseuds/memoriesofrain
Summary: Chris and Josh have been dating for a while now, but they haven't gone all the way yet.It's time to change that.





	Wanna Try Something With Me?

**Author's Note:**

> This was a blast to write, mostly the playful dialogue and just Chris and Josh being absolute goofballs.  
Day 16: Anal sex
> 
> I hope you all enjoy this!

Sometimes it seemed like half the advances they made in their relationship started as a result of alcohol. It was a random thought that passed through Chris’s head as he laid sprawled out on Josh’s couch, Josh mouthing at his jaw. Chris tilted his head to the side to let Josh continue his ministrations, the soft edges of the alcohol they’d been drinking adding a nice haze to the experience.

“Cochise, you taste funny,” Josh whispered against his ear.

Chris snorted unattractively and turned his head to look at Josh. “That’s where I put my cologne,” Chris informed him. Josh stuck his tongue out and blew a raspberry at him. He wrinkled his nose and playfully shoved at Josh’s face. “Ew, god really? Was that necessary?”

“Yes.”

He rolled his eyes, failing to control the grin on his face. “Oh is that so? You know what that calls for?”

“Pizza?”

He gave Josh a flat look. “No, we still have pizza in the kitchen.” He saw the way Josh’s eyes shot to the kitchen and wrapped his arms around the boy to prevent him from getting up. “That calls for revenge!”

Josh’s laugh echoed through the room as Chris zerberted Josh’s neck. The two fell into peals of laughter at the act, gasping for breath by the time they stopped laughing. Josh’s breath was hot against his neck and he could smell the beer Josh had been drinking just a few minutes ago.

The man hid his face against Chris’s neck, going back to placing kisses along the column of flesh. Josh nipped playfully at a spot before sucking on it garnering a groan from Chris. He knew he was going to have to cover that up tomorrow or at least wear a turtleneck so he wouldn’t get those teasing looks from their friend group.

After Josh seemed satisfied with the mark he’d made, he pulled away from Chris’s neck to look him in the eyes. “Hey, Chris?” Josh started, but he didn’t continue, seemingly stuck on what to say.

Chris shook the cobwebs from his brain and focused on Josh. “What’s up?” He asked casually. Josh sounded nervous and the last thing that Chris wanted Josh to feel was insecure or like he couldn’t talk to him. “You have the same look on your face as you did when you wanted to try blowjobs.” And proceeded to suck each other’s brains out through their dicks when they’d both agreed to try them.

Alcohol was their courage juice and it wasn’t like they drank a lot of it during these occasions, just a beer or two each.

“You uh- what would you say we took things a little further tonight?” Josh’s eyes had started to dart around him, never staying on Chris’s for longer than a second.

His face flushed and he studied Josh’s face. “You really want to?”

“Yeah I really do,” Josh was never really shy about what he wanted, even if he was nervous. “I was watching porn the other day and I want to try it.”

“You want to go further because you watched porn?” Honestly, this wasn’t even that big of a surprise to Chris. It was how Josh got a lot of his ideas for their relationship. At least it meant he was aware of what the act involved. “And you’re sure?”

Josh groaned and slapped at Chris’s chest. “Yes I’m sure I want to take it up the ass, Chris.”

He held his hands up in surrender. “Just making sure!” He gave Josh’s hips a little squeeze, running his thumbs against the sliver of skin that was visible in the space between Josh’s jeans and his shirt. “How do you want to do this?”

“What part of ‘I want it in the ass’ wasn’t clear?”

“Not that you doofus, do you really want to do this on your couch?”

“I mean… it _is_ a nice couch.”

He shook his head. “Alright, I’m overruling that, we’re not having our first time together be on this couch.” He gave Josh a pointed look. “No matter how nice it is.”

That just seemed to make Josh laugh as he scrambled to get up off Chris, grinning mischievously and purposefully grinding their erections together through their jeans. The moan that slipped out of Chris’s mouth only added to the other boy’s amusement.

“Jesus, Josh I thought you wanted to go further tonight,” Chris said, getting up from the couch.

“You saying you can’t last, Cochise?” Josh teased.

God his boyfriend was a little shit.

“Just because I half-assed it in gym doesn’t mean I’m not capable of tackling you to this floor.”

That roguish grin on Josh’s face didn’t fade at all. “Is that a promise?”

“Oh my god, let’s just go to your room.”

The bed was much comfier than the couch and within minutes they were both naked and making out again. This was something they were both well-versed in at this point and the familiarity soothed any of the nerves the might have had. When it seemed like they’d run out of air, Chris pulled broke the kiss with one final peck that had Josh giving him a lazy smile.

Chris fumbled with the side-table drawer moving crap aside to finally find the bottle of lube Josh had tucked in there. He grabbed a condom before he shoved the drawer haphazardly closed. He turned back to look at Josh only to snort at the sight of his boyfriend in the stereotypical ‘draw me like one of your French girls’ pose.

“Please don’t draw me, your drawings suck,” Josh said matter-of-factly.

“I can still leave you like this,” Chris warned, but he knew Josh was just needling him like usual.

His boyfriend gave a mock gasp. “I cannot believe you’d threaten such a thing, especially after I’ve offered you my ass.”

“You’re lucky you’re cute.”

“I’m adorable.” Josh rolled onto his back, grabbing his thighs and pulling them towards his chest, spreading them as best he could. “I’m not as flexible as that guy in the video…”

Chris didn’t agree with that statement at all. He had a perfect view of the most intimate parts of Josh. His hard cock was pressed against his stomach and Chris could see the smear of precum that was shiny along this belly button. The neat hair that framed the base of Josh’s cock and balls only adding to the pretty picture his boyfriend made. And then there was Josh’s ass.

He’d always liked Josh’s ass, but seeing it displayed like this, with his hole in full view of Chris made his cock jerk. “Fuck, Josh, do you know how good you look spread out like that?” Chris didn’t need an answer for that though, instead popping the cap off the bottle of lube and liberally coating his fingers. He went to put the bottle down, but he stopped and moved the bottle over to Josh’s hole and squirting a bit on it.

Josh jerked at the feel of the cold gel against his skin. “I don’t need to be wet to start this, you know that right?” Josh asked.

He shrugged his shoulders. “It can’t hurt to have a little more, can it?” Chris deposited the lube somewhere on the bed and moved his lubed fingers to Josh’s opening. “Tell me if I do anything wrong.”

“Chris, just put one in already.”

Listening to what Josh wanted, he slowly started pushing his finger in. Josh’s walls clamped down around his finger but Chris kept pushing it until it was all the way in. He didn’t move after that, letting Josh to the sensation until Josh gave him the okay. He leisurely began pumping his finger in and out, enjoying the interested noises Josh was making.

“Can I put another finger in?” Chris asked.

“Yeah just… go slow,” Josh said, with a small frown.

Chris didn’t move to put another finger in. “Am I hurting you?”

His boyfriend shook his head. “No, just feels weird. The guy in the video was enjoying it from the get go.”

“I thought you were enjoying it?”

“Oh I am,” Josh reassured, with a grin, “Just have to get used to it. See if you can find my prostate, heard it feels amazing.”

Chris decided to give Josh the benefit of the doubt and slipped another finger inside Josh’s hole. The channel was just as tight as it was when he’d put the first finger in and Chris felt his mind wander to what it those tight walls would feel like around his cock. The thought made Chris push his fingers a little harder into Josh, spreading them and then bending them to feel along the tight walls.

Josh jerked and moaned loudly when Chris hit the bundle of nerves inside him. “Oh fuck,” Josh cursed, his grip on his thighs getting tighter. “Chris do that again.”

Chris obliged, croaking his fingers and watching as Josh’s head tipped back and he let out another encouraging moan. He purposefully kept brushing against it and enjoying the way Josh was coming undone at his touch. “You like that?” Josh’s moans were a good enough answer to him. “I’m gonna slip another one in, okay?”

Josh spread his legs impossibly wider and Chris happily accepted the invitation. The third finger went in easier than the other ones and he was glad that Josh was relaxed enough to let him in. He was glad he’d used all that lube though because he doubted the slide would have been as good. He continued playing with Josh’s hole for a while longer, just listening as Josh seemed to grow more desperate with each moment that passed. When he finally felt like he couldn’t take the wait any longer, he pulled his fingers out of Josh’s entrance.

His boyfriend gave him a desperate look. “I hope you took those out so your dick can take its place,” he said in a breathy voice.

Chris was already sliding the condom onto himself. “Yeah, can’t wait anymore,” Chris mumbled. He guided his dick to Josh’s entrance, rubbing the tip against the winking hole. In one smooth movement he breached Josh, just enough so the head was spreading the rim wide.

Josh whined at the stretch, blinking his eyes rapidly but still giving Chris a smile. “Stretch feels good.”

Chris sent a smile back at him. “_You_ feel good.” With a tiny jerk of his hips he pushed in a little deeper, continuing this until he was fully seated to the hilt inside of Josh. Josh’s channel gripped around him like it was perfectly formed just for him and he said as much. “You fit like a glove.”

Josh hummed, finally letting his thighs go so he could wrap his legs around Chris’s waste. He pushed himself more against Chris, wiggling to see if he could get Chris’s cock to hit that wonderful bundle of nerves that felt so good. Chris got what Josh was trying to do and started thrusting shallowly in Josh, adjusting his angle every once in a while until he heard a choked moan come from Josh.

Chris chuckled, looking at the blissed out expression that was forming on his boyfriend’s face. “Found it,” he teased. He started thrusting in harder, his steady rhythm quickly devolving into frantic ones as he felt his orgasm grow closer and closer. He moaned Josh’s name, and shuddered as the channel around him tightened at the sound of Josh’s name on his tongue. “God, I’m close.”

“M-me too,” Josh panted, moving his hand down to tug at his hard cock.

“Then cum for me, Josh.”

And like magic, Josh was cumming against his belly, his eyes rolled back with a cry. Chris was quick to join him as Josh’s channel seemed to be trying to milk him dry.

They panted against each other, happy to bask in the afterglow of their orgasm. Chris slowly pulled himself out of Josh and slipped off the condom, tying it off and throwing it in the direction of the trashcan. He’d get it later. Now, it was time to just lie with his boyfriend.

“Aren’t you happy I suggested this?” Josh mumbled happily, snuggling against Chris shoulder.

“Yeah, I’m definitely happy about this,” Chris reassured, wrapping an arm around Josh’s waist and pulling him closer.

**Author's Note:**

> Thank you so much for reading! If you have time, I'd really appreciate it if you left a comment telling me what you thought of this. 
> 
> If you have any prompts you'd like me to write, please send them to my tumblr [cakelanguage](https://cakelanguage.tumblr.com/)


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